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Synthesis of 3,3-Dialkyl-Substituted Isoindolinones Enabled by Nickel-Catalyzed Reductive Dicarbofunctionalization of Enamides

Ke Fang, Wenyi Huang, Chunxiao Shan, Jingping Qu and Yifeng Chen*

*School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China, Email:

K. Fang, W. Huang, C. Shan, J. Qu, Y. Chen, Org. Lett., 2021, 23, 5523-5527.

DOI: 10.1021/acs.orglett.1c01871

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A nickel-catalyzed reductive dicarbofunctionalization of 1,1-disubstituted enamides with unactivated alkyl iodides provides 3,3-dialkyl-substituted isoindolinones. This tandem cyclization/reductive tolerates a broad range of functional groups. The use of a chiral Bn-Biox ligand induces excellent enantioselectivities.

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proposed mechanism

Key Words

isoindolinones, zinc

ID: J54-Y2021